Douglas Frantz
Washington University in St Louis, MO·Chemistry
Many drug molecules contain bonds between carbon and oxygen (C–O) or carbon and nitrogen (C–N). Some common ring-shaped building blocks, called N,O-heterocycles, hold nitrogen and oxygen atoms close together.
- Fields
Chemistry
- Topics
catalysis
organic chemistry
organic synthesis
- Grants
- 1 known grant, through Nov 2027
What they work on
- Discover and design metal-based catalysts that selectively form either C–O or C–N bonds when alkylating N,O-heterocycles, taming their ambident reactivity.
- Use high-throughput experimentation, quantitative reaction optimization and computational studies to understand what controls chemoselectivity and to optimize catalysts rationally.
- Develop catalytic alkylations that use non-traditional alkylating agents in place of genotoxic alkyl halides, across a wide range of drug-relevant heterocycles.
More about the research
When chemists try to attach a carbon group to these rings (an alkylation reaction), it can bond to either atom, giving unpredictable mixtures. This dual behavior is known as ambident reactivity. Because no reliable methods exist to control it, manufacturers often take longer, indirect routes, which raises the cost and environmental impact of making medicines.
Why it matters
Predictable control over C–O versus C–N bond formation could shorten manufacturing routes to life-saving drugs, lowering their cost and environmental footprint. It could also reduce reliance on genotoxic alkyl halides and extend to large-scale synthesis in the agrochemical and fine-chemical industries.
Known grants
From NIH and NSF research grants. Labs often have other funding we can't see.
Closest labs
Patrick Walsh
University of Pennsylvania, PA·Chemistry
Develop enantioselective nickel-catalyzed cross-electrophile coupling, which joins sulfur electrophiles with aryl or alkyl halides, to make diaryl and alkyl aryl sulfoxides enriched in one mirror-image form.
Tomislav Rovis
Columbia University, NY·Chemistry
Develop reactions that build nitrogen-containing rings (heterocycles) directly from simple feedstocks such as alkenes and alkanes, forming carbon–carbon and carbon–nitrogen bonds in one step without later manipulation.
Timothy Cernak
University of Michigan, MI·Chemistry·Early-career
Use graph theory, including adjacency matrix mapping of known total syntheses of terpenes, alkaloids and pharmaceuticals, to identify reaction types that do not yet exist but would be valuable for synthesis.
The school
Washington University in St Louis: 97 labs on PI Pages, $1.2B a year on research, 365 research doctorates a year.
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